Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:51:05 UTC
Update Date2021-09-14 15:40:03 UTC
HMDB IDHMDB0061149
Secondary Accession Numbers
  • HMDB61149
Metabolite Identification
Common NameHydroxyfluoroprednisolone butyrate
DescriptionHydroxyfluoroprednisolone butyrate, also known as HFB, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Hydroxyfluoroprednisolone butyrate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563999773
Synonyms
ValueSource
Hydroxyfluoroprednisolone butyric acidGenerator
HFBHMDB
Hydroxyfluoroprednisolone butyrateHMDB
Chemical FormulaC25H33FO7
Average Molecular Weight464.53
Monoisotopic Molecular Weight464.221031566
IUPAC Name(1R,2S,8S,10S,11S,14R,15S,17S)-1-fluoro-8,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl butanoate
Traditional Name(1R,2S,8S,10S,11S,14R,15S,17S)-1-fluoro-8,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl butanoate
CAS Registry Number1296177-38-2
SMILES
[H][C@@]12CC[C@](OC(=O)CCC)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](O)C2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C25H33FO7/c1-4-5-21(32)33-24(20(31)13-27)9-7-15-16-11-18(29)17-10-14(28)6-8-22(17,2)25(16,26)19(30)12-23(15,24)3/h6,8,10,15-16,18-19,27,29-30H,4-5,7,9,11-13H2,1-3H3/t15-,16-,18-,19-,22-,23-,24-,25-/m0/s1
InChI KeyKODYJDILUXBYNG-MXHGPKCJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • Steroid ester
  • 20-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 6-hydroxysteroid
  • Halo-steroid
  • 9-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Halohydrin
  • Fluorohydrin
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
logP2.08ALOGPS
logP1.67ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity117.92 m³·mol⁻¹ChemAxon
Polarizability47.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-239.00330932474
DeepCCS[M+Na]+213.81630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hydroxyfluoroprednisolone butyrate[H][C@@]12CC[C@](OC(=O)CCC)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](O)C2=CC(=O)C=C[C@]12C4135.9Standard polar33892256
Hydroxyfluoroprednisolone butyrate[H][C@@]12CC[C@](OC(=O)CCC)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](O)C2=CC(=O)C=C[C@]12C3200.9Standard non polar33892256
Hydroxyfluoroprednisolone butyrate[H][C@@]12CC[C@](OC(=O)CCC)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](O)C2=CC(=O)C=C[C@]12C3524.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxyfluoroprednisolone butyrate,1TMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3576.6Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,1TMS,isomer #2CCCC(=O)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3510.7Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,1TMS,isomer #3CCCC(=O)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3525.3Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,1TMS,isomer #4CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3567.9Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3488.9Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TMS,isomer #2CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3478.8Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TMS,isomer #3CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3525.0Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TMS,isomer #4CCCC(=O)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3440.8Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TMS,isomer #5CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3475.0Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TMS,isomer #6CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3466.2Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,3TMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3400.2Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,3TMS,isomer #2CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3409.7Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,3TMS,isomer #3CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3412.1Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,3TMS,isomer #4CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3387.9Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,4TMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3343.1Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,4TMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3479.7Standard non polar33892256
Hydroxyfluoroprednisolone butyrate,4TMS,isomer #1CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C)O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C3878.3Standard polar33892256
Hydroxyfluoroprednisolone butyrate,1TBDMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3829.9Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,1TBDMS,isomer #2CCCC(=O)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3724.6Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,1TBDMS,isomer #3CCCC(=O)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3739.7Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,1TBDMS,isomer #4CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3787.2Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TBDMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3955.2Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TBDMS,isomer #2CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3962.9Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TBDMS,isomer #3CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3976.7Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TBDMS,isomer #4CCCC(=O)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3899.5Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TBDMS,isomer #5CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C3918.5Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,2TBDMS,isomer #6CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C3903.4Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,3TBDMS,isomer #1CCCC(=O)O[C@]1(C(=O)CO[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C4098.9Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,3TBDMS,isomer #2CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C4093.1Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,3TBDMS,isomer #3CCCC(=O)O[C@]1(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C4107.5Semi standard non polar33892256
Hydroxyfluoroprednisolone butyrate,3TBDMS,isomer #4CCCC(=O)O[C@]1(C(=CO)O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C4066.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyfluoroprednisolone butyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyfluoroprednisolone butyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyfluoroprednisolone butyrate 10V, Negative-QTOFsplash10-03di-5002900000-daa0bdb997f422c9d6872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyfluoroprednisolone butyrate 20V, Negative-QTOFsplash10-07bk-8009200000-03ac1defadd37ddc8bd22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyfluoroprednisolone butyrate 40V, Negative-QTOFsplash10-0fr6-9006000000-45217a95b347b286bde42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyfluoroprednisolone butyrate 10V, Positive-QTOFsplash10-016s-1004900000-b7887c505cfff99563162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyfluoroprednisolone butyrate 20V, Positive-QTOFsplash10-016s-1029500000-cc1d1fabc5a870a74d152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyfluoroprednisolone butyrate 40V, Positive-QTOFsplash10-0006-5379000000-6ea04954c019b77ab6b02021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jamal KN, Callanan DG: The role of difluprednate ophthalmic emulsion in clinical practice. Clin Ophthalmol. 2009;3:381-90. Epub 2009 Jun 29. [PubMed:19668594 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.